4512-43-0Relevant articles and documents
Synthesis of cyclopentapeptides with three to five Aib units
Arnhold, Franziska S.,Linden, Anthony,Heimgartner, Heinz
, p. 232 - 244 (2015/03/04)
Four new Aib-containing cyclopentapeptides have been synthesized by cyclization of the corresponding linear pentapeptides using the diethyl phosphorocyanidate (DEPC)/EtN(iPr)2 method. The linear precursors were prepared via the 'azirine/oxazolo
Synthesis of poly-aib oligopeptides and aib-containing peptides via the 'azirine/oxazolone method', and their crystal structures
Dannecker-Doerig, Ingeborg,Linden, Anthony,Heimgartner, Heinz
, p. 993 - 1011 (2011/08/05)
The protected poly-Aib oligopeptides Z-(Aib)n-N(Me)Ph with n=2-6 were prepared according to the 'azirine/oxazolone method', i.e., by coupling amino or peptide acids with 2,2,N-trimethyl-N-phenyl-2H-azirin-3-amine (1a) as an Aib synthon (Schemea 2). Following the same concept, the segments Z-(Aib)3-OH (9) and H-L-Pro-(Aib)3-N(Me)Ph (20) were synthesized, and their subsequent coupling with N,N′- dicyclohexylcarbodiimide (DCC)/ZnCl2 led to the protected heptapeptide Z-(Aib)3-L-Pro-(Aib)3-N(Me)Ph (21; Schemea 3). The crystal structures of the poly-Aib oligopeptide amides were established by X-ray crystallography confirming the 310-helical conformation of Aib peptides.
